New York, New York, August 12- The 15th Annual Antigua & Barbuda Hamptons Challenge Regatta set sail on Saturday, August 9th, 2025, bringing the vibrant spirit of the Caribbean to Long Island’s shores. The race, held in Sag Harbor, featured a highly competitive fleet of sailing enthusiasts from across the region, all competing for the grand prize: an all-expenses-paid trip to Antigua to compete in Antigua Sailing Week 2026.
After a beautiful day of racing under near-perfect summer weather, the winning team was celebrated at a classy awards gala held at The Bell & Anchor. To promote community and empowerment, the event also featured a $5,000 donation from the Antigua and Barbuda Tourism Authority to i-tri, a local non-profit that builds confidence and resilience in middle school girls through triathlon training and mentorship.
“This regatta is more than just a race – it’s a celebration of the deep historical and cultural ties between Sag Harbor and English Harbor in Antigua,” said Hon. Charles Fernandez, Minister of Tourism, Civil Aviation, Transportation, and Investment for Antigua and Barbuda. “Both harbors are rich in maritime heritage, and this annual event beautifully showcases that connection while also building bridges between our communities.”
The Antigua & Barbuda Hamptons Challenge has become one of the most anticipated regattas in the Northeast, blending top-tier sailing with meaningful philanthropy and a display of Antiguan hospitality. Colin C. James, CEO of the Antigua and Barbuda Tourism Authority, highlighted the event’s significance to the island’s tourism strategy: “The Hamptons Challenge not only promotes Antigua and Barbuda as a premier sailing destination but also enables us to connect directly with travelers who appreciate culture, community, and world-class experiences. It’s always a privilege to bring a piece of Antigua to the Hamptons.”
Guests at the awards gala enjoyed a Caribbean-inspired evening featuring island cuisine, rum cocktails, and music, reflecting the warmth and vibrancy that Antigua and Barbuda is known for. The winning skipper, Lee Oldak, who led “Purple Haze” to victory, has competed in every race since it began and finally won on his 15th try. His crew received an all-expenses-paid trip to Antigua to participate in Antigua Sailing Week, one of the world’s most prestigious regattas.
As part of the weekend’s events, the ABTA hosted a lunch for VIP travel advisors from Long Island. Dean Fenton, U.S. Director for the Antigua & Barbuda Tourism Authority, addressed the guests – “I want to extend my heartfelt congratulations for the vibrant spirit of collaboration you have displayed throughout our time working together. As the Director of Tourism for the USA, I’ve seen firsthand how, as travel advisors, your dedication and personal connections help bring our islands to life for clients. I firmly believe that the strongest sales are built on relationships—not just transactions, and your role as trusted advisors offers the insight, creativity, and support that elevate our marketing and our destination in meaningful ways. Together, we continue to chart a course toward unforgettable experiences and lasting partnerships.”
In attendance for the multiple events over the weekend were the representatives from The Hut on Little Jumby Island, George Adams, Sophie Kirkpatrick, and Gary Randall from Blue Waters Resort & Spa. The storytelling about these establishments informed the media and travel advisors about the luxury offerings from both places.
As the sun set over Sag Harbor, participants and guests toasted to another successful year of racing, camaraderie, and cultural exchange, cementing the Antigua & Barbuda Hamptons Challenge as a cherished tradition with increasing influence.
